Reaction #2569

Reaction equation

N-methylmorpholine

isobutyl chloroformate

4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid

ammonia

→

title compound

Yield 50.9%

4-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

Yield 50.9%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureIn an atmosphere of argon and with cooling in an ice bath
2. 2
   Temperaturewas cooled in an ice bath
3. 3
   workup.WAITfollowed by additional 10 minutes
4. 4
   workup.STIRRINGof stirring at room temperature
5. 5
   ExtractionThe reaction mixture was extracted with methylene chloride
6. 6
   Dryingthe resulting organic layer was dried on anhydrous sodium carbonate
7. 7
   OtherThereafter, the solvent was removed by evaporation
8. 8
   Otherthe resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1)

Procedure

In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol). After 15 minutes of stirring at room temperature, 28% liquid ammonia (0.5 ml) was added to the reaction solution which was cooled in an ice bath, followed by additional 10 minutes of stirring at room temperature. The reaction mixture was extracted with methylene chloride, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1) to obtain 32 mg (50.9%) of the title compound in the form of light yellow oil.

Source